5 Powerful Questions to Ask Someone About Their Career

Questions to ask someone about their career

Do you work with employees who are unsure how to articulate their ambitions?  Career development conversations are an ideal opportunity to help them think creatively about their future success.  I have some powerful questions to ask someone about their career.  They will help them think about their future and open up possibilities. They are the questions that make up the Future Success Tool in the Career Conversation Toolkit.

What do we mean by “Future Success”?

Before we get to the questions I’d like to talk a little about the concept of “success”

Success means different things to different people. Everyone’s definition will be personal to them. Success doesn’t have to mean moving up in an organisation, taking on more responsibility, managing more people and a bigger budget.

When I talk about Future Success, people sometimes think I mean career goals or objectives. I don’t.

In fact, I think career goals and objectives can be quite limiting.  That is especially true if people use the SMART model developed for managing performance.

When people try and be SMART, they constrain themselves by describing success by position or job title. In other words, they define their career goal along the lines of “I want to be a [job title] by [date]” or “I want to be promoted to a [grade] by [date]”.

These goals are SMART in so much as they are Specific, Measurable, Attainable, Results-focussed and Timebound. But they are not particularly helpful because they limit options and possibilities.

The original purpose of SMART goals was to manage projects and performance. They assume predictability and a degree of influence and control. The way to make progress is to set a goal and then create a plan to work towards it. But does that scenario really apply when managing your career? Especially in an ever-changing organisation operating in an emergent, surprising world?

Future Success is quite different. Future Success is about describing intangible detail of how work will be when you have achieved your ambitions. At this stage, it doesn’t matter if it is realistic or not. Let’s face it, do we ever really achieve our ambitions? They’re always changing and evolving. They are like the horizon. They serve as a valuable guide and a direction, but as you make progress towards them so they continue to move ahead of you.

By describing the specifics of what work will be like you get beyond the simplicity and constraints created by a “job” or a “job title”. You focus on what you want your experience at work to involve. Which opens up all sorts of possibilities.

Questions to Ask Someone About Their Career

One way you can help employees think about their future is to ask them to imagine a miracle happens. For example, you could say:

Suppose you could wave a magic wand and develop your career in exactly the way you’d like….

What would you be doing day to day?

Where would you be working?

What kind of people would you be working with/for?

What would you be delivering or producing and who for?

Why is that important to you?

With each question, allow them lots of space to answer. There are no right or wrong answers. They can be as creative and as imaginative as they like as long as it’s something they would enjoy. Be curious. Try and build up a picture in your head of what they’re describing and ask whatever questions you need to ask to get the detail you need.

Future Success Questions in Practice

Let me give you an example of how these help in practice.

One of my clients, Mark, was a Client Services Director for an Advertising Agency and he had two people who both said they wanted to be Account Managers. The problem was there was only one role of Account Manager and it was already filled. I encouraged him to use the Future Success tool with each team member.

The next time we met, I asked him how he’d got on. He said “One team member, Kate, talked about working more with clients.  She wants to manage the team responsible for developing the whole ad campaign.  She saw herself chairing meetings with the client and leading on client presentations. She also wants to be doing more to develop the agency and how it’s run. She’s ambitious and she wants the challenge that comes with new roles and responsibilities.”  He went on to say, ” That’s great because I can give her opportunities to do all of those things to a great or lesser extent in her current role”.

What about the other team member? The answer? “Sam said she wanted more money. There’s nothing much I can do about that. She’s considering taking a year off to go traveling.”

Sure enough, Sam did leave shortly afterward. It seems she wasn’t committed to the organisation. But Kate embraced her new opportunities and responsibilities with relish. And when the opportunity arose, the decision to promote her into an Account Manager role was an easy one.

Future Success Tool

Click here to download a PDF of the Future Success tool.

Take Action

Interested in more questions to ask someone about their career? You can get this plus other powerful tools and questions as full colour postcards in the Career Conversation Toolkit.  You may also be interested in our Manager’s Guide to Career Conversations. Together, they will help you engage, retain and develop your employees through effective career conversations in 20 minutes or less.

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